Sort by
Relevancy

Free Stories

50%
Butterflies
There were a lot of good reasons to be out this early, but none as wonderful as seeing this first Giant Swallowtail awakening, and John smiled as it moved. Magnificent, he whispered, in awe of this giant as it slowly unfurled it's Forewings against the sun's morning warmth. It was, as they always we... Read full Story
shemale lover 2012-09-30 5,682 taboo transformation sex
66%
Fourth Slave
I had been to this particular establishment before. I knew very well what they did and the women here were nearly all abducted. I knew that. What had brought me here today or rather on this night, was the loss of my slave. I had sold her when I got bored with her. I had a particular taste in women t... Read full Story
shemale lover 2012-11-19 7,966 Stockings Fetish domination
100%
Angel Chapter 2
Angel Jones stepped off the train and hoped she was in the right place. It was noisy and confusing in the terminal, a far cry from the relatively quiet station in her home town where she had boarded the train that morning. One hand clutched a small suitcase that contained her makeup and clean linger... Read full Story
shemale lover 2012-11-30 4,189 oral sex tgirl feminization
100%
Claudia Coming out adventure part 1
*Author's Note: This story starts off being told in First person and after awhile the story shifts to third person* Hello everyone, my name is Claudia I am a Cross dresser who one day hopes to be transgendered, although I do not want the surgery, I am looking to eventually live my life full... Read full Story
MissClaudia 2015-01-04 5,864 tranny Stockings suck Creampie ass fucking doggy style Latex
88%
Seattle Weekend
Saturday morning and such a beautiful day nice and cool morning I went for a run. I consider myself in fairly good shape for my age but I try and make it to the top of a hill in our neighborhood. I get winded fairly quickly. Coming down the hill I ran into a nice looking athletic girl, maybe 38 year... Read full Story
Jon Paul 2018-08-09 9,985 Big Tits Cumshot Bareback Creampie Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
Florida TG Experience
I had known Jan from High School, we always had an attraction for each other but were dating someone else or married at the time. Jan had actually married a friend of mine and I was envious of course. She at that time had sandy blonde hair, and a body to die for. One evening we had them over for dr... Read full Story
Jon Paul 2018-08-13 10,815 Group Sex Big Tits Bareback Creampie Blowjob blonde Asian Ladyboy Shemale and Girl Guy Fucks Shemale Ass to Mouth cum in mouth double anal
100%
My Fantasy Story
My first time, Sissy Cuckold for BBC After ten years of marriage, my wife and I wanted more. First we went to some strip clubs together. One night one of the girls my wife liked told us about a swingers club. So we gave it a try. Best decision we'd ever made. We went, at first just wallflowers, ... Read full Story
Mikky666 2020-10-09 9,703 blonde Big Cock Interracial Ass to Mouth
100%
TG Girlfriend moves in
Monday morning 6:00 am and I am just awakening, and I realize a naked body beside me has her arm around me, we are both naked. My wife Lydia is out of town to a seminar, and this adorable brunette perky tits and lovely eyebrows, beautiful lips slightly pink, sleeping beside me. Joanne and I had spen... Read full Story
Jon Paul 2022-01-18 5,068 Amateur Cumshot Latina Masturbation Bareback Creampie Shemale Fucks Guy Blowjob Ladyboy Guy Fucks Shemale cum in mouth
100%
Tight Spot
XtinaSmith2017 Cody bit his lip as he looked over towards the shop, a little anxious about their planned endeavor but not wanting to come off as uncool to his friends, "Are you sure this is a good idea?" he asked. His friends grinned and laughed, playfully nudging him as they made their way ... Read full Story
Gwapo67 2022-07-22 5,751 Big Tits Bareback Creampie Shemale Fucks Guy Fetish Blowjob Big Cock Lingerie domination cum in mouth
100%
delicious virile male flesh
Tasted delicious virile male flesh… The breeze caressed my swollen nipples giving me pleasant shivers. The two glasses of Riesling had also contributed to my excitement. My crotch was burning as if the disappearing sun had blown all its thermal energy into me. Under my fine lace panties, purple o... Read full Story
hippocampus_171 2023-04-23 4,924 anal Small Tits Amateur Creampie Blowjob Mature small cock big ass feminisation cum in mouth gaycd virile
100%
The Bounty Hunter - Working With A Partner
My boss, Carl Bronson, was pleased with the results of my first case, and gave me more jobs over the next few months. In each, I learned from my mistakes and was able to apprehend my target. Even better, I was finally earning some good money and doing something that was worthwhile and, more importan... Read full Story
shemale lover 2012-01-29 4,378 sucking Creampie cum fucking
100%
Emily and Steve Part 10
It took me a long time to get over Emily, but like all pain, eventually it past and I started to want to get into a relationship again. Before Emily, I had gone out and hooked up with t-girls from the local scene a few times, but never thought of anything serious. My time with Emily had taught me... Read full Story
shemale lover 2012-04-08 3,304 anal sex Latina Creampie tgirl
100%
Serving Waitress
This is the first “didi” story I ever wrote. It’s my deepest (and darkest?) fantasy. It probably needs to be rewritten at some stage because I think it’s been written too much by my male brain and not enough by my female side. The story begins….. My wife, Susan, ... Read full Story
shemale lover 2012-08-28 4,730 anal sex Cumshot Creampie oral sex
66%
Dirty Black Summer Chapter 2
Back in the safety and seclusion of my mountain retreat later that afternoon, Summer and I sat back and drank a few beers to unwind, allowing the adrenaline and endorphins racing through our systems to subside somewhat. "I think we succeeded in getting inside his head a little," I told ... Read full Story
shemale lover 2012-09-25 4,323 tranny erection kissing
100%
Downsizing Chapter 3
Work was going quite well. The company started to grow again, and some new personnel had been hired. Even unknown to me, there had been a couple of males hired in the last few months. Ms. Stanton had informed them when she got to the dress code that the makeup was a requirement, and that the one mal... Read full Story
shemale lover 2012-11-10 2,980 anal sex Cumshot Creampie oral sex
87%
Anklets
This is my story. I'm a genetic woman in my .. *late* 40's . I was introduced to the TG world when I was a teenager... back then I was, and in some ways still am, a "tomboy trapped in a woman's body". I thought *girl clothes* were so ridiculous for ME to wear, that I put them on boys just ... Read full Story
shemale lover 2012-12-11 5,254 Creampie shemale oral
96%
The Backdoor
It was only my first time in the club and my hands were shaking beyond control. I almost didn't make it through the front door I was so nervous. I felt so out of place. Everywhere I looked, it felt like people were staring at me, judging me. It was like they knew I had no clue what I was doing. ... Read full Story
shemale lover 2013-01-03 16,490 sucking Shemale Fucks Guy Blowjob Big Cock Interracial
61%
Uncle's slutboy: the attack of the black men
On the way home from Grandpa would I through a park. Or I would not. but the road outside was sooo long and I felt frankly a bit sore and spent in the ass after being violated by gramps. so I shortcut through the park. After all it was not that bad. Not like those dank places without light and a lot... Read full Story
worshipbbc 2015-12-25 6,616 Creampie interracial sex ass fucking sissy
91%
The New Housemate's Secret
https://chyoa.com/chapter/Introduction.150836 The New Housemate's Secret How will you discover the hot new tenant's secret? Chapter 1 by Bauer1 The doorbell rings, a soft knocking accompanies the bell to break the silence of the house. You look up from your laptop nestled snuggly in your la... Read full Story
Acche 2019-04-04 21,886 Big Tits Cumshot Creampie Shemale Fucks Guy Blowjob Big Cock Guy Fucks Shemale handjob titfuck titjob cum in mouth
100%
Jon Story
When I learned we would be in Rio for a few days, I was overjoyed. Rio de Janeiro would have just what I was looking for. While on leave in Australia, I had developed a yearning for special girls, and through careful research, Rio seemed to be someplace very special indeed. It first started... Read full Story
shemale lover 2012-01-26 4,870 Creampie tits fucking big
33%
Being Barbi's Bitch
After ten wasted years of foolishly trusting in love to 'cure' me of my femininity, I had only just begun to re-embrace the sissy inside me when something made me reach out to an old friend. What made me do it, I really don't know. Although I was once again revelling in even the smallest aspects of ... Read full Story
shemale lover 2011-10-01 8,896 Stockings sucking domination
100%
Jamie is taken Part 2
Jamie came to on the cold dungeon floor retching and coughing, his mind paralyzed by a mixture of pleasure and panic. He had loved the orgasm he had just experienced. His experience with breathplay was less than half a day old and already he knew that he loved it almost as much as finally ... Read full Story
shemale lover 2011-11-30 3,885 Fetish bdsm fiction
100%
Jamie is taken Part 3
When this process was completed the Chinese gentleman s turned to his new acquisition in the floor. He lifted him up from the floor and deposited him on a high-backed chair; his legs still folded up, and tied him to it. Then he removed the strap from around his throat and instead shoved ... Read full Story
shemale lover 2011-11-30 6,314 Fetish domination bondage facefucking
0%
Lady Denisa's Gang Banged
The young black youth aged eighteen was lying on the bed while I mounted him for the third time that day. I used his cock and muscular body shamefully to bring myself off with no thought for his pleasure. Kenny was my toy boy, an aircraftsman from the base my husband commanded when he wasn't away on... Read full Story
shemale lover 2011-11-22 4,365 shemale oral orgasm
100%
A Fantasy - Part 2
Paula begins to grown, ohhing and ahhing. I suck hard and swirl my tongue around on the head of her cock. Sharon has pushed her dildo all the way into my ass and begins to pump my ass with a slow, steady rhythm. Paula holds my head in place and begins to thrust her cock into my mouth harder. "I'm go... Read full Story
swollenrooster 2023-09-20 4,904 Group Sex Cumshot Shemale Fucks Guy Shemale and Girl Guy Fucks Shemale shemale fucks shemale cum in mouth shemale fucks female
66%
The House of Lesslie
I. The mansion hadn't changed, not all that much, from how I remembered it. If at all, it had aged gracefully, as only English mansions can ¬ a massive Edwardian building that had served Lords and Ladies, had housed masters and servants for centuries. Around it, at a respectful distance, w... Read full Story
shemale lover 2011-10-14 5,493 pissing domination Latex
100%
Womanhood for Jenny Chapter 2
Despite the discomfort of her 'boob-job,' and the other surgeries, jenny had enjoyed their Caribbean 'vacation.' During the drive from the airport, she was impatient to show her friends the 'new jenny,' but felt the weariness of the return trip. She was happy when Master Charles pulled into their ow... Read full Story
shemale lover 2012-10-08 3,699 anal sex Cumshot cum swallowing boob job
50%
Magician's Assistant - Friends & Lovers Part 9
Magician's Assistant - Friends & Lovers takes place in the Magatrix the Magnificent Universe, which was first introduced in my serialized seven-part story, Magician's Assistant. The premise upon which both that story and this story are based revolves around the fact that Magatrix the Magnificent... Read full Story
shemale lover 2011-12-26 2,735 anal femdom erotic encounters
88%
Tipping Point -- Chapter 1: Blow by Blow
Chapter 1: Blow by Blow October 12th Thursday evening. Tick, tick tick... the minutes pass by while Nick lies on his back, staring at the white ceiling fan that hovers above. He raises his head, bats his eye lashes, and yawns. His long, wavy, auburn hair falls down his back with small curls. ... Read full Story
Danielle Pillory 2015-11-24 5,267 anal shemale domination spanking submission
75%
Something For Everyone Part 2
Josh was the first of the three to wake up. He left the two women in bed and took a long hot shower. The water felt good as it cascaded over his body, and he soon found himself wondering what was going to happen next. The sex had been fantastic, but it wasn't what he had been expecting. He finally d... Read full Story
shemale lover 2011-10-20 2,686 fingering oral sex stroking handjob
75%
Singapore tranny sex
My ship was dry-docked in Singapore for 3 weeks, n i was lucky enough to meet a gr8 girl first nite ashore, Lin, half chinese/ half malay, n fucking sexy. I slept at her flat most nites and the sex was awsome. She shared with a girl called Meena, a hostess on Singapore Airlines, but until this speci... Read full Story
shemale lover 2011-11-20 4,395 shemales Group Sex interracial sex
100%
Alabama Nan: Behind A Closed Doors
"How's Chinese?" I asked Karen. "That's fine Nan. Is this a real fancy place or what?" responded Karen from the bathroom. "It's your regular Mom and Pop, type restaurant. I'm going to dress casual." "Sounds fine by me?" said Karen. My stomach growl... Read full Story
shemale lover 2012-04-27 2,191 transsexual orgasm oral sex
83%
House Hunting Chrissie
When I casually mentioned to one of clients during a session that I was toying with the idea of perhaps buying a house and renting out my condo he needlessly took the time to remind that he owned one of the largest realty offices in town. It must a salesman thing, not being able to leave business ... Read full Story
shemale lover 2012-07-01 3,131 anal oral sex humor
100%
Hawaiian Morning TG Shemale
My clock radio said it was 6:35 in the morning. That means that my annoying alarm would start going off in fifteen minutes or so. But I didn't need an alarm clock to tell me about how my morning was going to be; I felt the playful movements of my beautiful Hawaiian lover behind me. She is a pet... Read full Story
shemale lover 2011-08-27 3,142 asshole Masturbation cum
28%
R Is For Roleplay
Chase Abernathy was exhausted. A combination of a heavy meal and a long flight had conspired to make him feel as if he’d just completed a triathlon. His shoulders ached from carrying his on-flight bags, his legs were sore from standing most of the day and his mind was numb from the effort o... Read full Story
shemale lover 2012-09-06 3,216 Cumshot Big Cock ass fuck
100%
caught crossdressing by my roommates
I am the monitor of my class and the president of the student union. On the surface, I looked glamorous, but I actually had an unknown secret - I would put on black stockings and boots every night in the dormitory and masturbate while watching pornographic movies. One day, my secret was revealed by ... Read full Story
Cdslutamy 2024-04-10 3,446 sissy
100%
Service Station
I had pulled off the M6 for a much-needed brew and a pit-stop. It was just gone 3am and I was on my way home to Preston from a meeting in London. I slid into a parking space, grabbed my overnight bag, and went into the Travelodge, booked in for one night, got a key, and went up to my room. I d... Read full Story
shemale lover 2011-08-25 2,498 suck shemale stroking
100%
Patrick's Treat
As usual, Maria entered my apartment as if she owned the place, slinging a bag down by the door and offering me a demure kiss. Her long dark hair had been pulled into cute bunches, one peeping out from either side of the back of her head. She was wearing a blue and white cheerleaders' uniform and wh... Read full Story
shemale lover 2011-10-04 3,489 jerking off deepthroating cum swallowing
100%
The Trip Part 3
I soaked in the tub for close to an hour, thinking about my predicament, it was only the second day of the trip, I figured if I was going to get through the week then I just had to resign myself and do whatever Joe asked of me, sex is just sex, I reasoned, it doesn’t matter who or how many peo... Read full Story
shemale lover 2012-05-20 3,550 anal sex Cumshot oral sex
85%
True story, TS 3-way
This is a true story. It was a typical night in Pattaya Thailand and I'm still recovering from the 25 hour flight from Tennessee to Bangkok that I flew just days before. After a few days in BKK, I arrange for a hotel car to me to Pattaya, a seedy explosion of lights, blaring music and drunken ... Read full Story
Thailover 2014-03-11 9,657 Cumshot threesome jerking ass fucking facial stroking
0%
Helplessly Bound
Hikaru slowly awoke from her deep slumber. She felt her head was so heavy, like having something had weakened her physically. Her vision was blurred and bit by bit slowly getting better, as she tried to investigate her surroundings. It was a dark room, only such a faint light so nothing could be ... Read full Story
shemale lover 2011-12-03 2,953 hardcore Sex Toys bondage
75%
Story for adults Part 4
Alice's place in the household proven to be quite complicated and very demanding. First and foremost she was Mistress Angela's slave and her needs came first. Pleasing and servicing Mistress Angela and Mistress Janice both sexually and otherwise took up a great deal of her time. Her life acquired a ... Read full Story
shemale lover 2011-12-20 4,260 bondage and discipline heavy feet reluctant
85%
Guarded Estate
I was a security guard at one of those flash Guarded estates where nothing exciting ever happened. My job was to patrol the estate at night on foot. I had taken the job to get away from the city and start afresh where no one knew me. I slept during the mornings and stayed inside my little house o... Read full Story
shemale lover 2012-02-13 3,055 Shemale Fucks Guy oral sex 69 pose
100%
A Christmas Tail Part 2
As I stepped off the elevator, following Angel into the room full of my ex-employee friends, I felt dazed, confused and incredibly embarrassed. They were all laughing hysterically at my maid's outfit. There were whistles and catcalls. I could hear various comments such as, "Well we can see t... Read full Story
shemale lover 2012-02-22 2,228 Fetish oral feminization
57%
He thought I didn't know
But although he was careful I found him out. There were the giveaway signs - a lack of interest in sex with me, hidden spunky hankies, that kind of thing. So I checked his internet use and found he'd been surfing shemale sites, pictures, stories and some nasty videos. He seemed to be fascinated ... Read full Story
shemale lover 2011-11-16 2,870 orgasm domination handjob
100%
Tony to Tanya
My name is Tony and I'm an average 19 year old boy. I'm 5 foot 7 inches tall, have shoulder-length brown hair and blue eyes. I often get mistaken as a girl from behind because of the length of my hair and because I look after it really well. I've been told I'm as good-looking as most girls my age. M... Read full Story
shemale lover 2011-12-19 4,224 cum dildo ass fucking
69%
Sales Training
Gary Michaels had been very successful in heating system sales during his first five years with his company, however the past two years had been very disappointing. So disappointing, in fact, that he had been called on the carpet and told to begin producing or else find another job. Gary really like... Read full Story
shemale lover 2013-07-21 5,042 Stockings Cumshot Lingerie oral sex crossdressing
100%
Dressed in holiday style Part 2
I was up by 1 p.m., showered, changed into some fresh panties and donned some hated boy clothes to hit the streets. I stopped by a local coffee shop (not the national chain-brand type) and over a mocha latte the barrista was kind enough to give me a few pointers about where she thought the best holi... Read full Story
shemale lover 2011-11-20 2,007 anal Stockings cum
50%
I am Baaack! Part 9
Rose stood before Joan's office door at 1:59pm. She was dressed in the same black leather outfit she had worn the night before, and she was also wearing the same "Don't fuck with me!" attitude. She had pulled herself together in the limo, assuming that Joan would have security cameras focu... Read full Story
shemale lover 2011-12-16 2,121 crossdressing erotic encounters fantastic
33%
Click, click, click....
Click, click, click…the sound of high heels contacting a hard surface has always attracted and aroused me. Whether it’s on tile floors in a hallway, the concrete of a parking ramp or the asphalt of a mall lot, I turn in anticipation to drink in some pleasing eye candy. How short will th... Read full Story
shemale lover 2012-06-09 5,195 anal Cumshot oral deepthroating
80%
Becoming Alanna Part 2
Walking into room number one, she told me kindly to strip nude and climb into the chair. I did as I was told and hopped in to the chair. I fit my feet and legs into the stirrups and she spread them apart exposing my cock balls and asshole. She looked me up and down and smiled "not much work wit... Read full Story
shemale lover 2012-07-12 3,821 sucking Fetish Ladyboy rimjob
100%
Darling Nikki
Chapter 1 - The Setup "I'm going to catch him!" Samantha thought to herself as she looked at her disheveled panty drawer. She now had proof that her roommate, Nick, had been wearing her clothes, but had to catch him in the act. She did a search online for ideas on how to catch him. She ... Read full Story
shemale lover 2012-07-15 7,304 Cumshot oral sex Latex sissy
100%
Fifties Housewife After the Party
I had not fallen asleep after Darren had, exhausted, after the party and the incredible lovemaking we had shared. I just couldn't come down from the high and emotions of the whole direction we had taken. I was lying spooned against him, his warm cock nestled warmly against my ass. My nightgown seeme... Read full Story
shemale lover 2012-08-03 3,482 anal sex Cumshot spanking
100%
When Rene Calls
Chapter One I first met Rene at an Art Museum Benefit. I aware of it at the time but Rene was the guest of honor as a result of his impending large donation to the museum's endowment fund. The reception and cocktail party was to be the event at which he was expected to announce his considerable... Read full Story
shemale lover 2012-09-14 2,768 tranny fuck oral
60%
The Pre-Nup Agreement
Several years ago one of Kellys' friends had a brother who was getting married in Reno and a bunch of us girls decided we would all get together for a wild weekend reunion. I unfortunately had several of my regular clients to see on Thursday and Friday afternoon and wouldn't be able to depart for ... Read full Story
shemale lover 2012-09-14 3,250 anal sex cum fingering oral sex deepthroating
100%
Lady In The House Ch. 06
A story by MicheleNylons (Michele continues to be used by prison inmates.) From Part V Harry leant over me and kissed me full on the lips. "That was worth every penny; you are one hot nurse," he laughed. Harry grabbed a handful of my clean white skirt and wiped his cock on it. The silver... Read full Story
✘Transensual✘ 2019-02-25 3,676 Crossdresser domination prisoner prison sex Prison Bitch